Dichloromethane → 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

반응식

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[CH:15][C:14]3[CH:17]=[N:18][N:19]([CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][O:21]4)[C:13]=3[CH:12]=2)C=[C:7]([O:9][CH3:10])[CH:8]=1.S(Cl)([Cl:29])(=O)=O.[CH2:31]([Cl:33])Cl>>[Cl:29][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[C:31]([Cl:33])[C:5]=1[C:11]1[N:16]=[CH:15][C:14]2[CH:17]=[N:18][N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)[C:13]=2[CH:12]=1

참가 물질

반응물 3

HCID 6344Dichloromethane

HCID 24648Sulfuryl chloride2회

HCID 867228186-(3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 867228196-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

실험 절차

At r.t. to a solution of 6-(3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.66 g, 1.9 mmol) in methylene chloride (10 mL) with stirring was added drop-wise sulfuryl chloride (300 μL, 3.7 mmol)(Acros Organics, Cat. No. 37815). The mixture was stirred at r.t. for 2 h. LCMS showed 25% product formed, and 75% was mono-chlorinated product. Additional sulfuryl chloride (100 μL) was added to the mixture. It was stirred at r.t. for 5 h, and then concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.78 g). LCMS (M+H)+=408.0.